JP2007513061A - 乱流条件下で反応混合物にシクロヘキサノンオキシムを混合することによってカプロラクタムを調製する方法 - Google Patents
乱流条件下で反応混合物にシクロヘキサノンオキシムを混合することによってカプロラクタムを調製する方法 Download PDFInfo
- Publication number
- JP2007513061A JP2007513061A JP2006529860A JP2006529860A JP2007513061A JP 2007513061 A JP2007513061 A JP 2007513061A JP 2006529860 A JP2006529860 A JP 2006529860A JP 2006529860 A JP2006529860 A JP 2006529860A JP 2007513061 A JP2007513061 A JP 2007513061A
- Authority
- JP
- Japan
- Prior art keywords
- reaction mixture
- tube
- mixing device
- cyclohexanone oxime
- cooler
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000011541 reaction mixture Substances 0.000 title claims abstract description 223
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 title claims abstract description 174
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 title claims abstract description 84
- 238000002156 mixing Methods 0.000 title claims abstract description 82
- 238000000034 method Methods 0.000 title claims abstract description 55
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 43
- 238000001816 cooling Methods 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 5
- 238000011144 upstream manufacturing Methods 0.000 claims description 5
- 235000011149 sulphuric acid Nutrition 0.000 claims description 4
- 229910003556 H2 SO4 Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000007788 liquid Substances 0.000 description 9
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
- 239000000908 ammonium hydroxide Substances 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000006237 Beckmann rearrangement reaction Methods 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 238000010924 continuous production Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000007696 Kjeldahl method Methods 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 230000000295 complement effect Effects 0.000 description 2
- -1 cycloalkyl brome Chemical compound 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/26—Nozzle-type reactors, i.e. the distribution of the initial reactants within the reactor is effected by their introduction or injection through nozzles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
- C07D201/02—Preparation of lactams
- C07D201/04—Preparation of lactams from or via oximes by Beckmann rearrangement
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F25/00—Flow mixers; Mixers for falling materials, e.g. solid particles
- B01F25/30—Injector mixers
- B01F25/31—Injector mixers in conduits or tubes through which the main component flows
- B01F25/312—Injector mixers in conduits or tubes through which the main component flows with Venturi elements; Details thereof
- B01F25/3121—Injector mixers in conduits or tubes through which the main component flows with Venturi elements; Details thereof with additional mixing means other than injector mixers, e.g. screens, baffles or rotating elements
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F25/00—Flow mixers; Mixers for falling materials, e.g. solid particles
- B01F25/30—Injector mixers
- B01F25/31—Injector mixers in conduits or tubes through which the main component flows
- B01F25/312—Injector mixers in conduits or tubes through which the main component flows with Venturi elements; Details thereof
- B01F25/3124—Injector mixers in conduits or tubes through which the main component flows with Venturi elements; Details thereof characterised by the place of introduction of the main flow
- B01F25/31242—Injector mixers in conduits or tubes through which the main component flows with Venturi elements; Details thereof characterised by the place of introduction of the main flow the main flow being injected in the central area of the venturi, creating an aspiration in the circumferential part of the conduit
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D223/08—Oxygen atoms
- C07D223/10—Oxygen atoms attached in position 2
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00164—Controlling or regulating processes controlling the flow
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Spinning Or Twisting Of Yarns (AREA)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP03076591 | 2003-05-23 | ||
EP03076589 | 2003-05-23 | ||
EP03076592 | 2003-05-23 | ||
EP03076590 | 2003-05-23 | ||
PCT/EP2004/005338 WO2004113287A1 (en) | 2003-05-23 | 2004-05-17 | Process for preparing caprolactam by admixture of cyclohexanone oxime to a reaction mixture under turbulent flow conditions |
Publications (1)
Publication Number | Publication Date |
---|---|
JP2007513061A true JP2007513061A (ja) | 2007-05-24 |
Family
ID=33479744
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006529862A Expired - Fee Related JP5014791B2 (ja) | 2003-05-23 | 2004-05-17 | カプロラクタムの調製方法 |
JP2006529860A Pending JP2007513061A (ja) | 2003-05-23 | 2004-05-17 | 乱流条件下で反応混合物にシクロヘキサノンオキシムを混合することによってカプロラクタムを調製する方法 |
JP2006529916A Expired - Fee Related JP5014792B2 (ja) | 2003-05-23 | 2004-05-17 | カプロラクタムを調製するための連続法 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006529862A Expired - Fee Related JP5014791B2 (ja) | 2003-05-23 | 2004-05-17 | カプロラクタムの調製方法 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006529916A Expired - Fee Related JP5014792B2 (ja) | 2003-05-23 | 2004-05-17 | カプロラクタムを調製するための連続法 |
Country Status (15)
Country | Link |
---|---|
US (3) | US7351820B2 (uk) |
EP (3) | EP1633706B1 (uk) |
JP (3) | JP5014791B2 (uk) |
KR (3) | KR101177137B1 (uk) |
CN (2) | CN1842519B (uk) |
AT (3) | ATE465991T1 (uk) |
BR (3) | BRPI0410604A (uk) |
DE (3) | DE602004032128D1 (uk) |
EA (3) | EA009600B1 (uk) |
MX (3) | MXPA05012688A (uk) |
MY (2) | MY139965A (uk) |
PL (1) | PL1628955T3 (uk) |
TW (3) | TWI335317B (uk) |
UA (1) | UA83663C2 (uk) |
WO (3) | WO2004103963A1 (uk) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102399188B (zh) * | 2010-09-10 | 2014-02-19 | 北京化工大学 | 一种贝克曼重排反应方法 |
WO2012141997A1 (en) | 2011-04-09 | 2012-10-18 | Amyris, Inc. | Process for preparing caprolactam and polyamides therefrom |
CN102229553B (zh) * | 2011-05-06 | 2012-10-10 | 清华大学 | 一种多段重排由环己酮肟制备己内酰胺的系统及方法 |
CN103007869B (zh) * | 2011-09-20 | 2015-02-25 | 中国石油化工股份有限公司 | 一种己内酰胺重排反应的三液相进料喷嘴 |
CN105085354B (zh) * | 2014-05-07 | 2018-09-28 | 中国石油化工股份有限公司 | 一种己内酰胺制备方法 |
TW202128630A (zh) | 2019-11-11 | 2021-08-01 | 荷蘭商卡普三世責任有限公司 | 工業規模上用於生產ε-己內醯胺及硫酸銨之方法及設備 |
CN115073343B (zh) * | 2022-06-29 | 2023-09-29 | 中国天辰工程有限公司 | 一种不副产硫酸铵的己内酰胺合成方法 |
Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3553204A (en) * | 1966-01-14 | 1971-01-05 | Inventa Ag | Process for the continuous manufacture of lactams |
JPS5170787A (ja) * | 1974-11-13 | 1976-06-18 | Allied Chem | Rakutamunoseizohoho |
JPS52135308A (en) * | 1976-05-07 | 1977-11-12 | Toa Nekken Kk | Mixer for emulsifying water and oil |
JPS5353687A (en) * | 1976-09-02 | 1978-05-16 | Stamicarbon | Production of lactam from cyclic oxime |
JPS5427579B1 (uk) * | 1968-04-11 | 1979-09-11 | ||
JPS5553266A (en) | 1978-10-16 | 1980-04-18 | Basf Ag | Continuous manufacture of epsilonncaprolactam by beckmann*s rearrangement |
JPS61138529A (ja) * | 1984-12-10 | 1986-06-26 | Idemitsu Petrochem Co Ltd | サイズ用乳化液の製造方法 |
JPH0664718U (ja) * | 1993-02-19 | 1994-09-13 | 敏克 清水 | ボルドー液の調製装置 |
JPH0699385B2 (ja) * | 1987-03-11 | 1994-12-07 | モンテディペ・ソチエタ・ペル・アツィオニ | ε−カプロラクタムの合成方法 |
JPH10180066A (ja) * | 1996-12-26 | 1998-07-07 | Jiinasu:Kk | 微粒化方法及びその装置 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2237365A (en) * | 1938-11-28 | 1941-04-08 | Ig Farbenindustrie Ag | Production of oximes |
US3914217A (en) * | 1974-11-13 | 1975-10-21 | Allied Chem | Process for the preparation of lactams |
US3953438A (en) * | 1975-02-07 | 1976-04-27 | Eli Lilly And Company | Preparation of cephalosporin ethers |
DE3642314A1 (de) * | 1986-12-11 | 1988-06-23 | Basf Ag | Verfahren zur herstellung von caprolactam durch beckmannsche umlagerung von cyclohexanonoxim |
JPH0737435B2 (ja) * | 1988-07-12 | 1995-04-26 | 三菱化学株式会社 | オキシム類の製法 |
EP0785188A4 (en) | 1995-07-20 | 1998-12-02 | Mitsubishi Chem Corp | METHOD FOR PRODUCING YPSILON CAPROLACTAM |
JPH1036332A (ja) * | 1996-07-22 | 1998-02-10 | Toray Ind Inc | シクロヘキサノンオキシム塩酸塩の精製方法 |
US6333411B1 (en) * | 1998-12-24 | 2001-12-25 | Praxair Technology, Inc. | Method for production of hydroxylammonium phosphate in the synthesis of caprolactam |
AU2001264408A1 (en) * | 2000-06-05 | 2001-12-17 | Dsm N.V. | Process for the production of cyclohexanone oxime |
US7005547B2 (en) * | 2000-06-05 | 2006-02-28 | Dsm Ip Assets B.V. | Process for the preparation of cyclohexanone oxime |
DE60138025D1 (de) * | 2000-06-05 | 2009-04-30 | Dsm Ip Assets Bv | Verfahren zur herstellung von cyclohexanonoxim |
JP4223694B2 (ja) * | 2001-03-28 | 2009-02-12 | 住友化学株式会社 | シクロヘキサノンオキシムの蒸発方法 |
US7141668B2 (en) | 2001-11-26 | 2006-11-28 | Dsm Ip Assets B.V. | Process for recovering caprolactam |
-
2004
- 2004-05-17 KR KR1020057022387A patent/KR101177137B1/ko active IP Right Grant
- 2004-05-17 EP EP04739241A patent/EP1633706B1/en not_active Expired - Lifetime
- 2004-05-17 BR BRPI0410604-0A patent/BRPI0410604A/pt not_active IP Right Cessation
- 2004-05-17 AT AT04739241T patent/ATE465991T1/de not_active IP Right Cessation
- 2004-05-17 KR KR1020057022403A patent/KR20060006088A/ko active Search and Examination
- 2004-05-17 MX MXPA05012688A patent/MXPA05012688A/es active IP Right Grant
- 2004-05-17 DE DE602004032128T patent/DE602004032128D1/de not_active Expired - Lifetime
- 2004-05-17 UA UAA200512399A patent/UA83663C2/uk unknown
- 2004-05-17 WO PCT/EP2004/005340 patent/WO2004103963A1/en active Application Filing
- 2004-05-17 BR BRPI0410587-7A patent/BRPI0410587A/pt active Search and Examination
- 2004-05-17 MX MXPA05012689A patent/MXPA05012689A/es active IP Right Grant
- 2004-05-17 EA EA200501850A patent/EA009600B1/ru not_active IP Right Cessation
- 2004-05-17 WO PCT/EP2004/005643 patent/WO2004103964A1/en active Application Filing
- 2004-05-17 CN CN2004800142488A patent/CN1842519B/zh not_active Expired - Lifetime
- 2004-05-17 EP EP04739353A patent/EP1628955B9/en not_active Expired - Lifetime
- 2004-05-17 US US10/557,771 patent/US7351820B2/en not_active Expired - Fee Related
- 2004-05-17 EP EP04739240A patent/EP1626953B1/en not_active Expired - Lifetime
- 2004-05-17 DE DE602004009173T patent/DE602004009173T2/de not_active Expired - Lifetime
- 2004-05-17 US US10/557,770 patent/US7358357B2/en active Active
- 2004-05-17 BR BRPI0410577-0A patent/BRPI0410577A/pt not_active IP Right Cessation
- 2004-05-17 KR KR1020057022348A patent/KR101199719B1/ko active IP Right Grant
- 2004-05-17 AT AT04739240T patent/ATE374179T1/de not_active IP Right Cessation
- 2004-05-17 US US10/557,753 patent/US7339056B2/en not_active Expired - Fee Related
- 2004-05-17 DE DE602004026866T patent/DE602004026866D1/de not_active Expired - Lifetime
- 2004-05-17 JP JP2006529862A patent/JP5014791B2/ja not_active Expired - Fee Related
- 2004-05-17 PL PL04739353T patent/PL1628955T3/pl unknown
- 2004-05-17 EA EA200501857A patent/EA010840B1/ru not_active IP Right Cessation
- 2004-05-17 MX MXPA05012621A patent/MXPA05012621A/es active IP Right Grant
- 2004-05-17 WO PCT/EP2004/005338 patent/WO2004113287A1/en active IP Right Grant
- 2004-05-17 EA EA200501858A patent/EA009914B1/ru not_active IP Right Cessation
- 2004-05-17 AT AT04739353T patent/ATE504564T1/de not_active IP Right Cessation
- 2004-05-17 JP JP2006529860A patent/JP2007513061A/ja active Pending
- 2004-05-17 JP JP2006529916A patent/JP5014792B2/ja not_active Expired - Fee Related
- 2004-05-17 CN CN201410381352.6A patent/CN104262223A/zh active Pending
- 2004-05-21 MY MYPI20041975A patent/MY139965A/en unknown
- 2004-05-21 MY MYPI20041968A patent/MY140436A/en unknown
- 2004-05-21 TW TW093114522A patent/TWI335317B/zh not_active IP Right Cessation
- 2004-05-21 TW TW093114520A patent/TWI337991B/zh not_active IP Right Cessation
- 2004-05-21 TW TW093114525A patent/TWI335318B/zh not_active IP Right Cessation
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3553204A (en) * | 1966-01-14 | 1971-01-05 | Inventa Ag | Process for the continuous manufacture of lactams |
JPS5427579B1 (uk) * | 1968-04-11 | 1979-09-11 | ||
JPS5170787A (ja) * | 1974-11-13 | 1976-06-18 | Allied Chem | Rakutamunoseizohoho |
JPS52135308A (en) * | 1976-05-07 | 1977-11-12 | Toa Nekken Kk | Mixer for emulsifying water and oil |
JPS5353687A (en) * | 1976-09-02 | 1978-05-16 | Stamicarbon | Production of lactam from cyclic oxime |
JPS5553266A (en) | 1978-10-16 | 1980-04-18 | Basf Ag | Continuous manufacture of epsilonncaprolactam by beckmann*s rearrangement |
JPS61138529A (ja) * | 1984-12-10 | 1986-06-26 | Idemitsu Petrochem Co Ltd | サイズ用乳化液の製造方法 |
JPH0699385B2 (ja) * | 1987-03-11 | 1994-12-07 | モンテディペ・ソチエタ・ペル・アツィオニ | ε−カプロラクタムの合成方法 |
JPH0664718U (ja) * | 1993-02-19 | 1994-09-13 | 敏克 清水 | ボルドー液の調製装置 |
JPH10180066A (ja) * | 1996-12-26 | 1998-07-07 | Jiinasu:Kk | 微粒化方法及びその装置 |
Non-Patent Citations (2)
Title |
---|
JPN6010072146; 化学大辞典 縮刷版,9巻, 1964, p.876 * |
JPN6013013489; 化学工学便覧 改訂六版, 19990225, 122-123頁、286-287頁, 丸善株式会社 |
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